HCID 68746959, compound → HCID 25191222, compound

HRID 388453Notes

Reaction equation

HRID 388453 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH3:29])[N:22]([CH3:30])[CH:21]=2)[C:9]1=[O:31])[CH2:5][CH2:6][CH3:7]>O1CCOCC1.O>[CH3:30][N:22]1[C:23]2[C:28](=[C:27]([CH3:29])[CH:26]=[CH:25][CH:24]=2)[C:20]([CH2:19][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17](=[O:18])[N:8]([CH:4]([CH2:5][CH2:6][CH3:7])[C:3]([OH:32])=[O:2])[C:9]2=[O:31])=[CH:21]1

Participants

4

Reactant 1

HCID 68746959HCID 68746959, compound

Product 1

HCID 25191222HCID 25191222, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester (108 mg, 0.25 mmol) in dioxane (2.5 ml) is added a solution of LiOH monohydrate (25 mg, 0.60 mmol) in H2O (2.5 mL). The solution is stirred at 60° C. for 16 hours. The reaction mixture is allowed to cool to room temperature, quenched with 4M HCl in dioxane (400 μl) and is concentrated. The resulting residue is triturated with MeoH and H2O to afford the title compound. LCMS (ESMS): m/z 420.21 (M+H+).

Workup

  1. temperatureto cool to room temperature
  2. customquenched with 4M HCl in dioxane (400 μl)
  3. concentrationis concentrated
  4. customThe resulting residue is triturated with MeoH and H2O

Sources & evidence

ORD record
ord-99a2da5ca6524f00ae71efba27ae1f49
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

Loading…